If you’ve ever wondered how to raise serious private money for real estate—even if you’re starting from scratch—you’ll find real inspiration and specific tactics in the success story of Tim Benskin.
On a recent episode of the Raising Private Money podcast, host Jay Conner sat down with Tim to unpack his journey. Tim, a member of Jay’s mastermind group, has already raised $940,000 in private money in less than a year, funding twelve deals since October 2023—all without using a single dollar of his cash.
Here are the game-changing takeaways from Tim’s experience and why they’re so actionable for anyone wanting to break into raising private money.
- Private Money Isn’t About Selling—It’s About Teaching
One of the standout points in Tim’s story is his approach to attracting private lenders. He doesn’t pitch or “sell” anyone. Instead, he takes pride in wearing a cap that says “Private Money Teacher,” because that’s exactly what he does—educates people about the opportunity for them to earn better returns on their money.
Most of Tim’s lenders had never even heard of private lending before. Some had their money sitting in savings accounts, earning modest interest, or in IRAs, but had no idea they could use those funds to lend on real estate. By patiently explaining the process and benefits, Tim creates trust and interest. The conversation is about helping, not selling, and that servant’s heart approach makes all the difference.
- Confidence Comes from Preparation
Tim and his wife Robin started by joining Jay Connor’s mastermind and immersing themselves in learning. They spent the first three months simply absorbing everything about raising private money. This education gave Tim the confidence to talk to potential lenders—with zero desperation or uncertainty.
A key lesson Tim shares: line up the money before you line up the deals. Having committed funds in advance lets you make more offers and move decisively, which is impossible if you’re scrambling for financing after finding a property. For Tim, this was the difference between sitting on the sidelines and closing twelve deals in under a year.
- Your Network Is Full of Potential Lenders (Even if They Don’t Know It Yet)
Tim’s first lender was a longtime friend and fellow church member. The introduction came through casual conversation, followed by inviting him to a webinar about private lending. The friend happened to already have a self-directed IRA—something Tim learned only by asking questions and listening.
The lesson? Don’t pre-judge or “pre-qualify” people based on assumptions. Many in your social and professional circles could become private lenders if you simply share what you’re doing and offer to teach them more. Tim’s story started with a breakfast meeting and a willingness to discuss his business openly—no hard sell necessary.
- Deal Structure: Win-Win for Both Sides
For his first deal, Tim purchased a distressed property in Rockford, Illinois, for $125,000, putting in $80,000 for renovations. The home’s value after improvements was around $250,000–260,000. Rather than flipping the home immediately, Tim found renters—again, through connections from his community—who take excellent care of the property.
His private lender is more than happy with solid returns that far exceed CD rates, all secured with real estate. The lender has earned nearly $20,000 in interest so far, with no roller-coaster stock market risks and no hidden fees.
- Growth Through Education and Consistency
Tim readily admits he started as an introvert, not a natural networker. But by consistently sharing what he knows, holding “lunch and learn” events, and always leading with education, both his confidence and his pool of lenders have grown. He emphasizes the tortoise-wins-the-race mentality—consistent effort, not quick sprints, leads to lasting success.
Bottom Line: You Can Do This Too
Tim Benskin is proof that you don’t need decades of experience or deep pockets to raise private money. If you’re willing to learn, educate others, and ask for conversations instead of pitching deals, you can build a business that works for you and your community of lenders. As Jay Conner says, “Every good deal starts with the money.”
If you want to dive deeper into the specifics, check out Tim’s full story and resources at www.StressFreeInvestingInformation.info, where you can even get a free copy of his book, Passive Income Without Tenants and Toilets. It might just be the blueprint you’ve been looking for.
10 Discussion Questions from this Episode:
- What were some of the biggest challenges Tim Benskin faced when he first started raising private money, and how did he overcome them?
- Jay and Tim both emphasize the importance of “teaching” rather than “selling” when approaching potential private lenders. Why do you think this strategy is effective in building trust?
- The episode discusses the role of self-directed IRAs in private lending. What advantages and disadvantages might this approach have for both lenders and investors?
- How did Tim’s network, such as his church community, play a role in successfully funding his first deals?
- Both Jay and Tim mention hearing advice at seminars to “get the deal under contract, and the money will show up.” Why do they disagree with this approach, and what do they suggest doing instead?
- What mindset shifts are necessary for new real estate investors to start successfully raising private money, according to this episode?
- How does securing private money before finding a deal impact an investor’s confidence and negotiating power?
- Tim mentions hosting “lunch and learns” and webinars to educate potential investors. What are the benefits of these educational events, and how might they influence prospective lenders?
- In the case study discussed, Tim details the numbers behind his first deal. What does this reveal about the real-world logistics and risks of private money-funded real estate investments?
- For someone just starting, what practical first steps do Jay and Tim recommend to begin raising private money, and why do they see mentorship and education as crucial parts of the process?
Fun facts that were revealed in the episode:
- The First Private Lender Was a Friend from Church
Tim’s first-ever private lender wasn’t a stranger or a big-time investor—it was a friend from his church who was also his wife Robin’s best friend’s husband! This goes to show you never know who in your existing network might be interested in private lending. - Private Money Pitch Over Breakfast
The conversation that kick-started Tim’s private lending journey happened casually over breakfast. Instead of a hard sales pitch, it was a friendly chat about real estate investing that led to a $125,000 investment. - Tim Wears a “Private Money Teacher” Cap—Literally!
Tim isn’t just metaphorically a teacher—he wears a cap embroidered with “Private Money Teacher” because his approach is all about educating, not selling, when talking to potential lenders. The hat has become part of his identity as a trusted resource.
Timestamps:
00:01 Raising $940K: Tim’s Strategy
06:13 Confident Real Estate Investments
06:54 Closing Deals with Private Money
11:20 Self-Directed IRAs for Real Estate
15:06 Surprise in Self-Directed IRA Discovery
17:23 Confidence Growth Since June ’23
22:09 Office Connection Leads to Housing Solution
25:56 Invest with Integrity: Contact Tim
26:39 Connect with Tim:
https://www.StressFreeInvestingInformation.info
608-346-2753
29:38 Private Money Real Estate Offer
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